In the summer of 2006, I was between my freshman and sophomore years of college. With no job and few friends left in my home town, I spent most of the summer driving across Michigan, crashing in friends’ living rooms (or kitchen floor, in one instance), occasionally happening on open mic nights or jam sessions or campfires where the acoustic guitar in my backseat would be of use.

My vehicle in those days was a late 90s Chrysler Town & Country that I inherited from my mom when she upgraded. The once mighty stock sound system was now neutered, its CD player rendered useless. Driving between cities, finding strong (and listenable) radio stations proved impractical.

All I had was a tape deck, and a garage sale copy of James Taylor’s Greatest Hits on cassette. Such was my soundtrack for that summer, and many months in between (it may have stayed in the deck as long as two years).

And while I usually pass on Greatest Hits compilations, when I found this the other day, I had to take it—and not just for the memories.

Around that period of my life, I would tell anyone who would listen that James Taylor was the greatest singer-songwriter that ever lived. And while I may have softened on that point for a while now, this collection of songs makes a pretty strong case.

These songs are filled with a tenderness that borders on fragility—a quality that informs all of the world’s best songwriters. . “Something in the Way She Moves,” “Fire and Rain” (his best song by a huge margin), and “Don’t Let Me Be Lonely Tonight” sound unassuming, but there’s a pain there that is just a margin away from overtaking him. “You’ve Got A Friend” offers anyone in that same bleak state what little hope he can, because he knows what it’s like to be without a friend (there’s a tragic, lived authenticity when he sings, “they’ll take your soul if you let them”). All this accompanied by some of the finest finger picked guitar parts put to tape.

When he’s not close to breaking, his songs are more pastoral. “Country Road,” “Carolina in My Mind,” and “Walking Man” are all odes to the simple life, finding joy in the countryside around him (which make for perfect driving songs).

Of course, not everything stands at the same level. This compilation has a few traces of schlock that infiltrated his more complete discography. Even as a more impressionable youth, “Mexico” was endured more than it was enjoyed. The live version of “Steamroller” is enjoyable, but is an oddly humorous turn for an incredibly emotive songwriter.

Even still, those tracks are tied strongly enough to my memories of those long drives to have value for me. And this album will forever be tied to enthusiastic reunions, cheap roadside food stops, and long drives through backroads under the star-filled Michigan sky.